On Sept. 10, 1923, Ernest Hemingway received his first assignment as a journalist for the Toronto Star.

He was put on an overnight train to Kingston, Ont., to report on a daring prison break by five inmates earlier that day. The five desperate rogues had set fire to hay in the prison stables to produce a smokescreen they could escape under. They used a homemade ladder to scale the wall and one of the guards was bashed in the head with the handle of a pitchfork. The most famous of the escapees was Norman (Red) Ryan, whom the Canuck press would eventually dub the “Jesse James of Canada” and a “master criminal.”

Ryan is also the subject of Calgary journalist and filmmaker Jim Brown’s new book, The Golden Boy of Crime: The Almost Certainly True Story of Norman Red Ryan.

Well, sort of. This is no ordinary true-crime book and there is more than a hint of irony in that title.

The coverage provided by Hemingway, and many other journalists of the day, is actually key to the book’s true focus. Because no matter how exciting the actual escape may have been, the future author of The Sun Also Rises and Old Man of the Sea felt the need to embellish. He described Ryan as a “thick, freckle-faced man whose prison cap could not hide his flaming head” before identifying Red’s fellow escapees as Young Brown, Big Simpson, Runty Bryans and Wyoming McMullen.

“When I first found out that Hemingway had written about this guy, I thought ‘That’s kind of cool. That will be interesting,’ ” says Brown, in an interview from his Calgary home. “Then, reading Hemingway’s coverage of Red Ryan’s jail break from Kingston, I discovered he just made up nicknames for all of the other convicts that escaped with him. He just made them up. I thought: ‘This is hilarious, this is absolutely great.’ It’s like novel writing on the front page of the paper.”

On the back cover of Golden Boy of Crime, there is a more accurate assessment of Red Ryan. He was “Canada’s most overrated bank robber.” He was also a liar, a thief, a coward, a cop killer and, by most accounts in the book, nowhere near a criminal mastermind.

Still, the book is not really an expose on Ryan himself. The bloom has long been off that particular rose thanks to the criminal’s disastrous attempt to rob a Sarnia, Ont., liquor store in May of 1936, which resulted in not only his own death but also that of a young police officer he shot four times.

Ryan’s return to crime followed a baffling, stranger-than-fiction rise to fame in Canada. Over the years, he charmed politicians, priests, wardens, doctors, the public and even a prime minister. All were responsible in one way or another in making Ryan one of the first Canadians to be granted parole. They were convinced he had been reformed into a good Christian while in prison, where he busied himself lecturing hardened criminals about the folly of their lives while lamenting his own lost years. After the shooting death, most changed their tune, including Prime Minister R.B. Bennett. He had visited Ryan in prison and, depending on who you believe, may have greatly helped expedite his release.

But while the press descended on numerous people involved in Ryan’s release to comment on his treacherous return to crime, no journalist accepted any responsibility for the media’s role in both relentlessly mythologizing his earlier criminal exploits and selling the myth that he had been redeemed in prison.

Which is what ultimately interested Brown about the whole saga. When approached by Harper Collins to write the book, he admits he had little desire to pen a biography about a bank robber. But another angle emerged as he started doing research.

Jim Brown, author of The Golden Boy of Crime: The Almost Certainly True Story of Norman Red Ryan. Courtesy, Harper Collins.Calgary

“I started reading all of the coverage from back when he was active,” Brown says. “I was just mesmerized by how bad the journalism was. It just seemed like this was a particularly good time to be writing about bad journalism because what we do gets such a bad rap right now and everyone always seems to be lamenting about the state of journalism. I thought, ‘Wow, they have no idea about how bad it could be.’ This guy was such a liar and the reporters just wrote down everything he said and everything that was said about him and reported it as fact and maybe a couple days later did another story saying ‘Don’t believe any of those other stories you’ve been reading, but you can believe this one.’ It was just crazy, the stuff they were making up. And everyone was doing it.”

A case in point would be a small piece in the Nov. 8, 1923, edition of the Toronto Daily Star, which reported on Ryan’s supposed return to Toronto as if he were a movie star. According to the story, Ryan roguishly took a sweetheart to a roller-skating rink despite being “much sought by the Toronto Police.” In fact, Brown would discover, Ryan would have been on the lam in Minnesota at the time.

Brown has been a journalist for 30 years, starting in print before moving to CBC Radio. Examining the often-strange overlap between fact and fiction has always been a pet interest for the journalist and broadcaster. Radiant City, the 2006 film he made with fellow Calgarian Gary Burns, was a comical and thought-provoking twist that seemed to comment on non-fiction cinema just as much as it did suburban sprawl.

“Playing with the form always interests me,” Brown says.

So while the broad strokes of Ryan’s story are told, Brown fills the book with a number of intriguing off-road excursions. There’s a great bit on Hemingway’s acrimonious split from the Star and his toxic relationship with his hated editor Harry Hindmarsh. There’s a humorous snapshot of “Toronto the Good,” where Brown describes his former hometown’s prudish history and inherent dullness. He uses Ryan’s story to offer some amusing if occasionally deep thoughts about the true nature of morality. He dedicates a good deal of space not only to this particular tale but the process of writing a true-crime story in general.

In the end, Brown seems to land on a somewhat depressing conclusion about Ryan. Not one of the characters who hovered around the criminal was driven by pure motives. Ryan may have manipulated people, but those who abetted him were also ruthlessly self-serving. They weren’t moved by goodness when it came to convincing others of Ryan’s supposed reformation. They wanted to sell papers, or further their political careers, or advance ideas of prison reform, or simply seek publicity for themselves.

In short, Brown doesn’t give anyone a free ride when it comes to the almost certainly true story of Norman Red Ryan.

“Show me someone from that story that deserves a free ride,” he says with a laugh. “They were all in it up to their eyeballs.”

The Golden Boy of Crime: The Almost Certainly True Story of Norman Red Ryan is in stores May 14.